Sodium hydride → 6-Benzyl-2-chloro-4-(3-methoxypropoxy)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 80816Notes

Reaction equation

HRID 80816 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][OH:6].[H-].[Na+].[CH2:9]([N:16]1[CH2:27][CH2:26][C:19]2[N:20]=[C:21]([Cl:25])[N:22]=[C:23](Cl)[C:18]=2[CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)(C)(C)C.C1COCC1>[CH2:9]([N:16]1[CH2:27][CH2:26][C:19]2[N:20]=[C:21]([Cl:25])[N:22]=[C:23]([O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:18]=2[CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 741163-Methoxy-1-propanolHCID 378190156-Benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido(4,3-d)pyrimidine

Product 1

HCID 866902656-Benzyl-2-chloro-4-(3-methoxypropoxy)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-methoxypropan-1-ol (0.500 mL, 5.23 mmol) in t-butanol (5 mL) was added a 60% dispersion of NaH in oil (70 mg, 1.75 mmol). The resulting suspension was permitted to stir for 30 minutes at which time the reaction was placed at 0° C. and charged with 6-benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (CAS#778574-06-4, 300 mg, 1.02 mmol) as a solution in THF (1.5 mL). After 20 minutes the mixture was quenched with saturated aqueous NH4Cl, and diluted with ethyl acetate and water. The layers were then separated and the organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The resulting residue was purified via silica gel flash chromatography to provide 6-benzyl-2-chloro-4-(3-methoxypropoxy)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. MS (ESI+) m/z 348.1 (M+H)+.

Workup

  1. customwas placed at 0° C.
  2. customAfter 20 minutes the mixture was quenched with saturated aqueous NH4Cl
  3. additiondiluted with ethyl acetate and water
  4. customThe layers were then separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified via silica gel flash chromatography

Sources & evidence

ORD record
ord-025f72b6e2794e8b8517cad22b076c4c
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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